Benzenesulfonamides having a nitrogen-containing substituents on the benzene ring are known as being herbicidal. For example, U.S. Pat. No. 4,369,058 discloses herbicidal benzenesulfonamides of the general formula ##STR2## where R.sub.1 is H, Cl, Br, F, C.sub.1 -C.sub.4 alkyl, OCH.sub.3 or NO.sub.2 ; and
R.sub.2 is NCO, NHCO.sub.2 R.sub.3, NHCOSR.sub.3, NHCOR.sub.3, NHCONR.sub.4 R.sub.5 or NR.sub.6 R.sub.7. PA1 European Patent Application (EP-A) No. 102,924 discloses herbicidal azidobenzenesulfonamides of the formula ##STR3## where R.sub.1 is H, halo, NO.sub.2, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl or C.sub.2 -C.sub.5 alkoxyalkoxy. PA1 R.sub.1 is NR.sub.4 R.sub.5, N(CH.sub.3)OR.sub.6, NHCN, NRA, P(W)R.sub.4 (W.sub.1 R.sub.5), P(W)(W.sub.1 R.sub.4)(W.sub.2 R.sub.5), P.sup.+ (C.sub.6 H.sub.5).sub.3, P.sup.+ R.sub.6 R.sub.7 R.sub.8, SR.sub.9, SO.sub.2 R.sub.9, C(R.sub.10)(R.sub.11)NO.sub.2, CH(CN).sub.2 or Q; PA1 Q is ##STR5## R.sub.2 is H, F, Cl, Br, OCH.sub.3, OC.sub.2 H.sub.5, OCF.sub.2 H, SCH.sub.3, N(CH.sub.3).sub.2, NO.sub.2, CH.sub.3 or CF.sub.3 ; PA1 R.sub.3 is H, F, Cl, Br, C.sub.1 -C.sub.4 alkyl, CO.sub.2 R.sub.15, NO.sub.2, CF.sub.3, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, SO.sub.2 NR.sub.16 R.sub.17, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 alkylsulfonyloxy, C.sub.2 -C.sub.5 alkoxyalkyl or C.sub.3 -C.sub.4 alkenyloxy; PA1 R.sub.4 and R.sub.5 are independently C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkyl substituted by 1 atom of Br or 1-3 atoms of F or Cl, C.sub.3 -C.sub.5 alkenyl, C.sub.3 -C.sub.5 cycloalkyl, OH, OCH.sub.3, CH.sub.2 OH, CH.sub.2 OR.sub.6, or CH.sub.2 CH.sub.2 OR.sub.6 ; or PA1 R.sub.4 and R.sub.5 may be taken together as --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --(CH.sub.2).sub.2 O(CH.sub.2).sub.2 --; PA1 R.sub.6 is C.sub.1 -C.sub.6 alkyl; PA1 R.sub.7 and R.sub.8 are independently C.sub.1 -C.sub.4 alkyl; PA1 R.sub.9 is C.sub.1 -C.sub.4 alkyl, phenyl or phenyl substituted with 1-3 atoms of F, Cl or 1 Br; PA1 R.sub.10 and R.sub.11 are independently H, C.sub.1 -C.sub.4 alkyl, phenyl or phenyl substituted with 1 atom of Br or 1-3 atoms of F or Cl; PA1 R.sub.12 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or NHR.sub.9 ; PA1 R.sub.13 and R.sub.14 are independently H, C.sub.1 -C.sub.3 alkyl, OR.sub.6, SR.sub.6, NHC(O)R.sub.6, F, Cl, Br or CO.sub.2 R.sub.6 ; PA1 R.sub.15 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, CH.sub.2 CH.sub.2 Cl or CH.sub.2 CH.sub.2 OCH.sub.3 ; PA1 R.sub.16 and R.sub.17 are independently C.sub.1 -C.sub.2 alkyl; PA1 W is O or S; PA1 W.sub.1 and W.sub.2 are independently O, S or NH; PA1 A is ##STR6## X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, F, Br, I, OCF.sub.2 H, CH.sub.2 F, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3 or CF.sub.3 ; PA1 Y is H, C.sub.1 -C.sub.3 alkyl, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, CH.sub.2 OCH.sub.2 CH.sub.3, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, ##STR7## OCF.sub.2 H, SCF.sub.2 H or cyclopropyl; m is 2 or 3; PA1 L.sub.1 and L.sub.2 are independently O or S; PA1 R.sub.18 is H or CH.sub.3 ; PA1 Z is CH or N; PA1 Y.sub.1 is O or CH.sub.2 ; PA1 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; and PA1 Y.sub.2 is H or CH.sub.3 ; PA1 (a) when X is Cl, F, Br or I, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H; PA1 (b) when either X or Y is OCF.sub.2 H, then Z is CH; and PA1 (c) when Q is Q-11 or Q-12, then R.sub.13 is other than H; PA1 (1) Compounds of Formulae I or II where R is H and A is A-1; PA1 (2) Compounds of Preferred 1 where X is CH.sub.3, OCH.sub.3 or Cl and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or CH.sub.2 OCH.sub.3 ; and PA1 (3) Compounds of Preferred 2 where R.sub.2 is H, Cl, CH.sub.3 or OCH.sub.3 and R.sub.3 is Cl, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, NO.sub.2, CO.sub.2 (C.sub.1 -C.sub.3 alkyl), SO.sub.2 N(CH.sub.3).sub.2, OSO.sub.2 CH.sub.3, OSO.sub.2 C.sub.2 H.sub.5, SO.sub.2 CH.sub.3, SO.sub.2 C.sub.2 H.sub.5 or allyloxy.
The present invention provides a novel class of benzenesulfonamides.